The Singlehood Series: An Embarrassing Encounter With My Date’s Daughter Left Me With A Bruised Ego

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I’m not really the one to judge anyone about their past so when this girl I met on Twitter told me she had a daughter, I didn’t think much of it. She was also very clear that she didn’t want anything serious since things hadn’t ended well with her baby daddy. For me, I liked her and that was the most important thing. She checked all my boxes and we had an instant connection from the first day we met. The thing that attracted me to her the most was her aura. She oozed confidence and sex appeal.

“What man would leave you, surely?” I asked her on one of our many dates.

She chuckled then replied, “I think I was too much woman for them.”

“You’ll never be too much for me, babe.”

For the next couple of weeks, I got to know Lauren deeper. She opened up about raising her daughter as a single mother and how her journey has been. She also explained that she doesn’t like bringing men home because she doesn’t want to give her daughter the wrong impression. I understood her situation and for the next month or so we would go over to my house over the weekend when her daughter was with her father.

Our relationship flourished and got more serious than both of us expected. I was ready to settle down with Lauren and we talked about moving in together. Naturally, we were nervous about how her daughter would take a strange man hanging out with her mom. I was extremely nervous about meeting her and kept pushing the date forward.

“You can’t avoid it forever.” Lauren reminded me.

“I know, but this is a big step for both of us,” I said.

From the stories she told me, her daughter seemed like a firecracker. At only 5 years old, she could articulate herself better than many adults I know of. She was a bright student and as outgoing as her mother. She was very attached to her and the two were like best friends. Additionally, she took it upon herself to be the chairman of her mom’s boyfriend vetting committee and her word was final. This was one of the reasons Lauren never brought me to her place until she was confident that her daughter would like me.

“I’ve told her so much about you.” She said.

“How did she take it that you’re dating?”

“At first, she wasn’t for it. But she saw how happy I’ve been lately so she’s open to the idea.”

“Sometimes, I forget you’re talking about at 5-year-old girl.” I paused “Can I bribe her with chocolate? I know how her mommy loves chocolate.”

“Trust me, she’s not your average girl. Besides, her father literally gives her everything she wants. You’re going to have to try harder than that.”

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It got to a point that I was having sleepless nights thinking about how to win over a child. I didn’t think finding the girl of my dreams would be an uphill task but she was worth it. My married friends advised me to just be myself but for me, that wasn’t good enough. I had to go big or go home.

So, I decided to throw her daughter a random party and called it the “Meet Mommy’s Boyfriend Party”. No one else had done it so that already set me apart from the rest. There I was searching for the ins and outs of the internet for a small party theme for children. Everything didn’t match the standard I wanted so once again, I took matters into my own hands.

Since I worked in the entertainment industry, I used my connections to get one of the most famous musicians in the country to show up at Lauren’s house and sing for her. Lucky for me, he agreed and didn’t even charge me anything. Everything was going according to plan and looked promising except for one small mistake –  I didn’t ask her mom if I could have the party. I wanted it to be a surprise for both of them. In fact, I lied to her.

“You know you’re meeting Apryl in a few days.” She said.


“Have you come up with something?”

“I decided to take you both to this nice restaurant.”

“Oh… Nice and simple. I like that.”

The much anticipated day came and my plan was still on track. So far, things were going well. I had made reservations and my colleagues complimented my suit.  Then, the musician rang me at around 6 pm.  I thought he was about to give me some bad news but he simply asked if he could get a lift to the restaurant. I agreed and he showed up barely ten minutes later. Every time I waited for something to go wrong, it just became better which made me more nervous.

As we headed to the restaurant, chaos ensued. I had a brush with a bus driver that cost me a good 20 minutes. On the other hand, this musician realized he had left his violin in the office so we had to go back and get it. By the time we were on the road again, it was way past 7 o’clock. My reservation was for 7.30 pm and at this restaurant, they only gave you the reservation if you’re all there.

Lauren called me frantically when she was asked to wait until everyone had arrived.

“I can’t believe you’re late. This is so unlike you.”

“I’m sorry, babe. I’ll explain when I get there. I’m 10 minutes away.” I explained.

As soon as she hung up, I called the restaurant and explained my predicament. They agreed to hold the table for another 5 minutes but Lauren and her daughter were still waiting at the lounge. Finally, I arrived with the musician and we made our way in. We bumped into Lauren on our way in and the two gave each other an awkward stare.

“Do you know each other?” I asked.

No one said anything. I thought Lauren was star struck until her daughter broke the ice.

“Look, mom. It’s your old boyfriend.”

It turns out Lauren has a thing for guys in the entertainment industry and had dated this guy. In fact, it looked like it was quite serious as Apryl took a particular liking to him over me. I was like an awkward third wheel on my own date as he serenaded them with his violin to the delight of other diners. Long story short, Lauren broke up with me a week after and was seen on a date with the musician. This might be my jealousy talking but I didn’t even like her that much.

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The singlehood series is a collection of real-life stories and opinions from different people. It looks at the current world of dating in Kenya and experiences that people have gone through. The views and opinions expressed here are those of the contributors and do not necessarily represent or reflect the views of